ES2242044T3 - Sintesis mejorada de un intermedio de ceftiofur. - Google Patents

Sintesis mejorada de un intermedio de ceftiofur.

Info

Publication number: ES2242044T3
Authority: ES; Spain
Prior art keywords: acid; acetate; reaction; thiomethyl; cefem
Prior art date: 2002-01-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES02751578T

Other languages

English (en)

Spanish (es)

Inventor

Pramod Narayan Deshpande

Bhausaheb Pandharinath Khadangale

Surulichamy Senthil Kumar

Gautam Kumar Das

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Orchid Pharma Ltd

Original Assignee

Orchid Chemicals and Pharmaceuticals Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-01-04

Filing date

2002-08-13

Publication date

2005-11-01

2002-08-13 Application filed by Orchid Chemicals and Pharmaceuticals Ltd filed Critical Orchid Chemicals and Pharmaceuticals Ltd

2005-11-01 Application granted granted Critical

2005-11-01 Publication of ES2242044T3 publication Critical patent/ES2242044T3/es

2022-08-13 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

ZBHXIWJRIFEVQY-IHMPYVIRSA-N ceftiofur Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC(=O)C1=CC=CO1 ZBHXIWJRIFEVQY-IHMPYVIRSA-N 0.000 title claims description 9
229960005229 ceftiofur Drugs 0.000 title claims description 9
230000015572 biosynthetic process Effects 0.000 title description 5
238000003786 synthesis reaction Methods 0.000 title description 5
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims abstract description 32
238000000034 method Methods 0.000 claims abstract description 24
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims abstract description 17
229910015900 BF3 Inorganic materials 0.000 claims abstract description 16
238000009833 condensation Methods 0.000 claims abstract description 13
230000005494 condensation Effects 0.000 claims abstract description 13
239000000203 mixture Substances 0.000 claims abstract description 12
239000003960 organic solvent Substances 0.000 claims abstract description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 51
239000002253 acid Substances 0.000 claims description 23
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 6
ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical group [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 claims description 3
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
229910052796 boron Inorganic materials 0.000 claims description 3
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 3
229940011051 isopropyl acetate Drugs 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 3
239000003791 organic solvent mixture Substances 0.000 claims 2
239000002904 solvent Substances 0.000 abstract description 7
238000002360 preparation method Methods 0.000 abstract description 2
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 abstract 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
-1 alkali metal salts Chemical class 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
239000010410 layer Substances 0.000 description 4
229910052979 sodium sulfide Inorganic materials 0.000 description 4
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
229930186147 Cephalosporin Natural products 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
239000002585 base Substances 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
LKYIPGJOXSVWPX-UHFFFAOYSA-M sodium;thiophene-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CC=CS1 LKYIPGJOXSVWPX-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)
Steroid Compounds (AREA)

ES02751578T 2002-01-04 2002-08-13 Sintesis mejorada de un intermedio de ceftiofur. Expired - Lifetime ES2242044T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US35178		2002-01-04
US10/035,178 US20030135041A1 (en)	2002-01-04	2002-01-04	Synthesis of ceftiofur intermediate

Publications (1)

Publication Number	Publication Date
ES2242044T3 true ES2242044T3 (es)	2005-11-01

Family

ID=21881126

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES02751578T Expired - Lifetime ES2242044T3 (es)	2002-01-04	2002-08-13	Sintesis mejorada de un intermedio de ceftiofur.

Country Status (12)

Country	Link
US (2)	US20030135041A1 (fr)
EP (1)	EP1463734B1 (fr)
KR (1)	KR100847339B1 (fr)
CN (1)	CN1310923C (fr)
AT (1)	ATE294183T1 (fr)
AU (1)	AU2002367103A1 (fr)
BR (1)	BR0215473A (fr)
CA (1)	CA2471310C (fr)
DE (1)	DE60203944T2 (fr)
ES (1)	ES2242044T3 (fr)
MX (1)	MXPA04006587A (fr)
WO (1)	WO2003055893A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100502390B1 (ko) *	2001-09-07	2005-07-19	주식회사 엘지생명과학	세팔로스포린산 유도체의 제조방법
CA2503885A1 (fr) *	2002-10-29	2004-05-13	Lupin Limited	Procede de fabrication de ceftiofur
US8470809B2 (en) *	2005-10-12	2013-06-25	Orchid Chemicals & Pharmaceuticals Limited	Crystalline sodium salt of cephalosporin antibiotic
EP1934231A4 (fr) *	2005-10-12	2011-10-26	Orchid Chemicals & Pharm Ltd	Sel de sodium cristallin d'antibiotique a base de cephalosporine
WO2010020871A2 (fr) *	2008-08-22	2010-02-25	Orchid Chemicals & Pharmaceuticals Limited	Sel de sodium cristallin de l'antibiotique céphalosporine
CN102234289B (zh) *	2010-05-02	2013-07-10	青岛科技大学	一种头孢噻呋中间体新的制备方法
CN103804394A (zh) *	2014-01-24	2014-05-21	瑞普（天津）生物药业有限公司	一种头孢噻呋中间体的制备方法
CN108623617B (zh) *	2017-03-22	2021-04-02	蒋辉	一种头孢噻呋中间体的制备方法
CN112645965B (zh) *	2020-12-22	2022-03-25	浙江华尔成生物药业股份有限公司	一种真空冻干注射用头孢噻呋钠的制备工艺
CN114409676A (zh) *	2021-12-24	2022-04-29	河南立诺制药有限公司	一种7-acf的制备方法
CN116535421A (zh) *	2023-07-04	2023-08-04	齐鲁晟华制药有限公司	头孢噻呋钠的合成方法
CN117964641A (zh) *	2023-12-07	2024-05-03	河北和煜药业科技有限公司	一种头孢噻呋中间体7-acf的制备方法
CN118561869B (zh) *	2024-08-05	2024-10-08	齐鲁晟华制药有限公司	一种头孢噻呋钠的合成方法

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1565941A (en) *	1977-02-08	1980-04-23	Toyama Chemical Co Ltd	Process for producing 7-(substituted)amino-3-substituted thiomethyl cephem carboxylic acids
US4144391A (en) *	1977-03-07	1979-03-13	Eli Lilly And Company	Cephalosporin displacement reaction
US4115645A (en) *	1977-05-10	1978-09-19	Eli Lilly And Company	Decolorizing process for 7-amino-3-(((2-methyl-1,3,4-thiadiazol-5-yl)thio)methyl)-3-cephem-4-carboxylic acid
FR2472574A1 (fr)	1979-12-24	1981-07-03	Ici Pharma	Derives de cephalosporine et composition pharmaceutique les contenant
FR2479229B1 (fr)	1980-03-26	1986-01-17	Clin Midy	Nouveaux derives des cephalosporines, leur procede de preparation et les medicaments utilisables comme antibiotiques qui contiennent lesdits derives
US4472574A (en) *	1981-05-22	1984-09-18	Hoffman-La Roche Inc.	Process for the manufacture of a cephem carboxylic acid derivative
AT384222B (de) *	1985-06-03	1987-10-12	Biochemie Gmbh	Verfahren zur herstellung von 7-amino-3alkoxymethyl-3-cephem-4-carbonsaeuren
DE3650526T2 (de)	1985-08-12	1996-10-31	Upjohn Co	Umwandlung des cephalosporin-hydrohalid-salzes zu einem alkalimetallsalz
GB9115287D0 (en)	1991-07-15	1991-08-28	Antibioticos Spa	Process for the preparation of cephalosporins intermediates
AT401177B (de) *	1993-10-22	1996-07-25	Biochemie Gmbh	Verfahren zur herstellung von 7-amino-3-cephem-4-carbonsäure-derivaten
IN184690B (fr) *	1996-03-18	2000-09-23	Ranbaxy Lab Ltd
KR0176013B1 (ko) *	1996-07-19	1999-03-20	성재갑	세펨유도체의 제조방법
IN189046B (fr) *	1998-03-30	2002-12-14	Ranbaxy Lab Ltd
IN189047B (fr) *	1998-06-01	2002-12-14	Ranbaxy Lab Ltd
US6384213B1 (en) *	1998-10-23	2002-05-07	Ranbaxy Laboratories Limited	Process for preparing a pure, pharmacopoeial grade amorphous form of cefuroxime axetil
US6191123B1 (en) *	1999-03-19	2001-02-20	Parker Hughes Institute	Organic-arsenic compounds
JP2003505485A (ja)	1999-07-30	2003-02-12	ランバクシーラボラトリーズリミテッド	フォームｉセリプロロールヒドロクロリドの改良形態
IN190849B (fr)	2000-07-17	2003-08-23	Ranbaxy Lab Ltd
US6458949B1 (en) *	2000-08-14	2002-10-01	Aurobindo Pharma Limited	Ceftiofur, its intermediate and a process for the preparation of the same
US6476220B2 (en)	2000-11-27	2002-11-05	Aurobindo Pharma Limited	Process for the preparation of furaca
WO2002094816A1 (fr)	2001-05-18	2002-11-28	Aurobindo Pharma Limited	Procede de cristallisation du losartan potassium

2002
- 2002-01-04 US US10/035,178 patent/US20030135041A1/en not_active Abandoned
- 2002-08-01 US US10/208,879 patent/US6803461B2/en not_active Expired - Fee Related
- 2002-08-13 EP EP02751578A patent/EP1463734B1/fr not_active Expired - Lifetime
- 2002-08-13 AU AU2002367103A patent/AU2002367103A1/en not_active Abandoned
- 2002-08-13 WO PCT/IB2002/003268 patent/WO2003055893A1/fr not_active Ceased
- 2002-08-13 DE DE60203944T patent/DE60203944T2/de not_active Expired - Lifetime
- 2002-08-13 MX MXPA04006587A patent/MXPA04006587A/es active IP Right Grant
- 2002-08-13 KR KR1020047010492A patent/KR100847339B1/ko not_active Expired - Fee Related
- 2002-08-13 CA CA2471310A patent/CA2471310C/fr not_active Expired - Fee Related
- 2002-08-13 CN CNB028266498A patent/CN1310923C/zh not_active Expired - Fee Related
- 2002-08-13 ES ES02751578T patent/ES2242044T3/es not_active Expired - Lifetime
- 2002-08-13 BR BR0215473-0A patent/BR0215473A/pt not_active IP Right Cessation
- 2002-08-13 AT AT02751578T patent/ATE294183T1/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
US20030130502A1 (en)	2003-07-10
CA2471310C (fr)	2011-02-22
CN1310923C (zh)	2007-04-18
US6803461B2 (en)	2004-10-12
CN1639169A (zh)	2005-07-13
EP1463734A1 (fr)	2004-10-06
AU2002367103A1 (en)	2003-07-15
KR20040098628A (ko)	2004-11-20
MXPA04006587A (es)	2005-07-13
DE60203944T2 (de)	2006-02-23
DE60203944D1 (de)	2005-06-02
ATE294183T1 (de)	2005-05-15
US20030135041A1 (en)	2003-07-17
KR100847339B1 (ko)	2008-07-21
BR0215473A (pt)	2004-11-30
CA2471310A1 (fr)	2003-07-10
WO2003055893A1 (fr)	2003-07-10
EP1463734B1 (fr)	2005-04-27

Publication	Publication Date	Title
US7825241B2 (en)	2010-11-02	Cefdinir intermediate
ES2242044T3 (es)	2005-11-01	Sintesis mejorada de un intermedio de ceftiofur.
US6388070B1 (en)	2002-05-14	Thioester derivatives of thiazolyl acetic acid and their use in the preparation of cephalosporin compounds
JP4152879B2 (ja)	2008-09-17	結晶性セフジニル酸付加塩及びこれを用いたセフジニルの製造方法
JP2009530268A (ja)	2009-08-27	（１−オキサ−又は１−チア−）３−セフェム誘導体及び関連する中間体の調製方法
ES2624675T3 (es)	2017-07-17	Nuevo proceso de preparación de la ceftarolina fosamil
KR100671881B1 (ko)	2007-01-19	세팜 유도체로부터의 페남 유도체 제조방법
UA76761C2 (uk)	2006-09-15	Спосіб синтезу тропенолу для його одержання в промисловому масштабі
JP3751880B2 (ja)	2006-03-01	高純度セフポドキシムプロキセチルの製造方法
JP4022070B2 (ja)	2007-12-12	新規チアゾール化合物およびその製造方法
ES2310011T3 (es)	2008-12-16	Proceso para producir compuestos de 3-cefem.
WO2003059908A1 (fr)	2003-07-24	Nouveaux derives thioester et procede de preparation de cephalosporine
US4284767A (en)	1981-08-18	Process for preparing 3-carbamoyloxymethyl cephalosporins
US20060149055A1 (en)	2006-07-06	Process for the manufacture of cefpodoxime proxetil
JP2003511455A (ja)	2003-03-25	７−アミノ−３−メトキシメチル−３−セフェム−４−カルボン酸の製造方法
WO2003059914A1 (fr)	2003-07-24	Synthese amelioree d'intermediaire de ceftiofur
US7662955B2 (en)	2010-02-16	Process for the preparation of cefoxitin
US4304909A (en)	1981-12-08	Process for producing 7-(D(-)-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-α-(4-hydroxyphenyl)acetamido)-3-(5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl)-.DELTA.3 -cephem-4-carboxylic acid and a pharmaceutically acceptable salt thereof
US6500963B2 (en)	2002-12-31	Process for preparing optically active dihydropyrones
KR20030066204A (ko)	2003-08-09	세프디토렌 중간체의 제조방법
KR20240090633A (ko)	2024-06-21	트리아졸로피리미디논 유도체의 제조방법
CN104163803B (zh)	2017-01-04	一种头孢洛林酯的合成方法
EP0382220A2 (fr)	1990-08-16	Préparation de dérivés d'acide aminothiazolylacétique
NZ206984A (en)	1986-12-05	The manufacture of 7-(imidazol-2-yl)-amino-3-(1h-1,2,3-triazol-4-yl)-thiomethylceph-3-em-4-carboxylic acid
JPH0354108B2 (fr)	1991-08-19